JPS62500588A - 置換アミノ除草剤製造の改良方法 - Google Patents

置換アミノ除草剤製造の改良方法

Info

Publication number: JPS62500588A
Authority: JP; Japan
Prior art keywords: carbon atoms; amine; alkyl; hydrogen; carried out
Prior art date: 1984-10-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP60504706A

Other languages

English (en)

Japanese (ja)

Inventor

ポミドー，パトリシア　ビー

ワード，カール　イー

Original Assignee

シエブロン　リサ−チ　コンパニ−

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-10-26

Filing date

1985-10-24

Publication date

1987-03-12

1985-10-24 Application filed by シエブロン　リサ−チ　コンパニ− filed Critical シエブロン　リサ−チ　コンパニ−

1987-03-12 Publication of JPS62500588A publication Critical patent/JPS62500588A/ja

Status Pending legal-status Critical Current

Links

125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 5
239000004009 herbicide Substances 0.000 title description 9
238000004519 manufacturing process Methods 0.000 title description 8
238000000034 method Methods 0.000 claims description 79
125000004432 carbon atom Chemical group C* 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 38
150000001412 amines Chemical class 0.000 claims description 37
150000001875 compounds Chemical class 0.000 claims description 33
-1 indenyl-1-yl Chemical group 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 18
230000008569 process Effects 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000002947 alkylene group Chemical group 0.000 claims description 11
125000004429 atom Chemical group 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
229940126062 Compound A Drugs 0.000 claims description 9
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 9
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000006413 ring segment Chemical group 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 5
239000007864 aqueous solution Substances 0.000 claims description 5
125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
239000000376 reactant Substances 0.000 claims description 5
150000003512 tertiary amines Chemical class 0.000 claims description 5
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000002346 iodo group Chemical group I* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical group [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 claims description 2
150000003335 secondary amines Chemical class 0.000 claims description 2
239000000126 substance Substances 0.000 claims 5
150000003973 alkyl amines Chemical class 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
125000000262 haloalkenyl group Chemical group 0.000 claims 1
125000004438 haloalkoxy group Chemical group 0.000 claims 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
239000000203 mixture Substances 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 12
239000007858 starting material Substances 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
230000002363 herbicidal effect Effects 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000000047 product Substances 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
241000196324 Embryophyta Species 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
150000003141 primary amines Chemical class 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000000926 separation method Methods 0.000 description 3
JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000594009 Phoxinus phoxinus Species 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
238000005576 amination reaction Methods 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000004428 fluoroalkoxy group Chemical group 0.000 description 2
239000006260 foam Substances 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
230000008635 plant growth Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
PEHUTKMBCZECOQ-UHFFFAOYSA-N 2-(1h-inden-1-yl)-5-(methylamino)-4-[3-(trifluoromethyl)phenyl]furan-3-one Chemical compound O=C1C(C2C3=CC=CC=C3C=C2)OC(NC)=C1C1=CC=CC(C(F)(F)F)=C1 PEHUTKMBCZECOQ-UHFFFAOYSA-N 0.000 description 1
OZHHDYQJUGTLLZ-UHFFFAOYSA-N 2-[7-(fluoromethyl)-3-methoxy-5-nitronaphthalen-1-yl]-5-(methylamino)-4-[3-(trifluoromethyl)phenyl]furan-3-one Chemical compound O=C1C(C=2C3=CC(CF)=CC(=C3C=C(OC)C=2)[N+]([O-])=O)OC(NC)=C1C1=CC=CC(C(F)(F)F)=C1 OZHHDYQJUGTLLZ-UHFFFAOYSA-N 0.000 description 1
CYWLMIHFRLDNBA-UHFFFAOYSA-N 2-[8-methoxy-3-methyl-2-(trifluoromethyl)naphthalen-1-yl]-5-(methylamino)-4-[3-(trifluoromethyl)phenyl]furan-3-one Chemical compound O=C1C(C=2C3=C(OC)C=CC=C3C=C(C)C=2C(F)(F)F)OC(NC)=C1C1=CC=CC(C(F)(F)F)=C1 CYWLMIHFRLDNBA-UHFFFAOYSA-N 0.000 description 1
NVDUCCRVKSUGCB-UHFFFAOYSA-N 2-ethylsulfanyl-n-methylethanamine Chemical compound CCSCCNC NVDUCCRVKSUGCB-UHFFFAOYSA-N 0.000 description 1
FZMCOUGLSYNQOF-UHFFFAOYSA-N 2-methyl-5-(methylamino)-4-[3-(trifluoromethylsulfanyl)phenyl]furan-3-one Chemical compound O=C1C(C)OC(NC)=C1C1=CC=CC(SC(F)(F)F)=C1 FZMCOUGLSYNQOF-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
GPJSMBYRBBFXMB-UHFFFAOYSA-N 4-(3-bromo-2-ethylphenyl)-5-(methylamino)-2-naphthalen-1-ylfuran-3-one Chemical compound CCC1=C(Br)C=CC=C1C1=C(NC)OC(C=2C3=CC=CC=C3C=CC=2)C1=O GPJSMBYRBBFXMB-UHFFFAOYSA-N 0.000 description 1
UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
DAXBGWSOKGFORQ-UHFFFAOYSA-N 5-(methylamino)-2-(trifluoromethyl)-4-[3-(trifluoromethyl)phenyl]furan-3-one Chemical compound O=C1C(C(F)(F)F)OC(NC)=C1C1=CC=CC(C(F)(F)F)=C1 DAXBGWSOKGFORQ-UHFFFAOYSA-N 0.000 description 1
NYRMIJKDBAQCHC-UHFFFAOYSA-N 5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3(2H)-one Chemical compound O1C(NC)=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1 NYRMIJKDBAQCHC-UHFFFAOYSA-N 0.000 description 1
FKGNAEBAFUNRHS-UHFFFAOYSA-N 5-[methoxymethyl(methyl)amino]-2-methyl-4-[3-(trifluoromethyl)phenyl]furan-3-one Chemical compound O=C1C(C)OC(N(C)COC)=C1C1=CC=CC(C(F)(F)F)=C1 FKGNAEBAFUNRHS-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical group [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
241001072332 Monia Species 0.000 description 1
UWCKZWKVTKZRAP-UHFFFAOYSA-N N-methyl-2,3-dihydrofuran-5-amine Chemical compound CNC1=CCCO1 UWCKZWKVTKZRAP-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
244000250129 Trigonella foenum graecum Species 0.000 description 1
241001464837 Viridiplantae Species 0.000 description 1
159000000021 acetate salts Chemical group 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000005456 alcohol based solvent Substances 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003684 drug solvent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
230000008570 general process Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000003114 inden-1-yl group Chemical group [H]C1=C([H])C([H])(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
NJRWPMOKVNBWCX-UHFFFAOYSA-N methyl 2-iminoacetate Chemical compound COC(=O)C=N NJRWPMOKVNBWCX-UHFFFAOYSA-N 0.000 description 1
FGQSMXLNUMMHOR-UHFFFAOYSA-N methyl methanimidate Chemical compound COC=N FGQSMXLNUMMHOR-UHFFFAOYSA-N 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
IOXXVNYDGIXMIP-UHFFFAOYSA-N n-methylprop-2-en-1-amine Chemical compound CNCC=C IOXXVNYDGIXMIP-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
238000005457 optimization Methods 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)

JP60504706A 1984-10-26 1985-10-24 置換アミノ除草剤製造の改良方法 Pending JPS62500588A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US66607884A	1984-10-26	1984-10-26
US666078		1984-10-26

Publications (1)

Publication Number	Publication Date
JPS62500588A true JPS62500588A (ja)	1987-03-12

Family

ID=24672730

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60504706A Pending JPS62500588A (ja)	1984-10-26	1985-10-24	置換アミノ除草剤製造の改良方法

Country Status (8)

Country	Link
US (1)	US4663466A (pt)
EP (1)	EP0198054A1 (pt)
JP (1)	JPS62500588A (pt)
KR (1)	KR870700616A (pt)
AU (1)	AU4962385A (pt)
BR (1)	BR8507011A (pt)
IL (1)	IL76847A0 (pt)
WO (1)	WO1986002643A1 (pt)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU570466B2 (en) *	1983-06-17	1988-03-17	Rhone-Poulenc Agro	3-oxo-2,3-dihydrofuran derivatives
WO1997002263A1 (en) *	1995-06-30	1997-01-23	Korea Research Institute Of Chemical Technology	3(2h)-furanone derivatives
KR0119908B1 (ko) *	1994-04-18	1997-10-30	강박광	3(2h)-푸란온 유도체
CN105669613B (zh) *	2016-01-12	2018-07-27	江苏明化合晟生物科技有限公司	高效除草剂呋草酮的生产方法
CN107056735B (zh) *	2017-05-24	2019-06-25	江苏省农用激素工程技术研究中心有限公司	呋草酮中间体的制备方法

1985
- 1985-10-24 JP JP60504706A patent/JPS62500588A/ja active Pending
- 1985-10-24 EP EP85905372A patent/EP0198054A1/en not_active Withdrawn
- 1985-10-24 WO PCT/US1985/002082 patent/WO1986002643A1/en not_active Ceased
- 1985-10-24 AU AU49623/85A patent/AU4962385A/en not_active Abandoned
- 1985-10-24 BR BR8507011A patent/BR8507011A/pt unknown
- 1985-10-28 IL IL76847A patent/IL76847A0/xx unknown
- 1985-11-25 US US06/801,273 patent/US4663466A/en not_active Expired - Fee Related
1986
- 1986-05-12 KR KR860700263A patent/KR870700616A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
US4663466A (en)	1987-05-05
WO1986002643A1 (en)	1986-05-09
EP0198054A1 (en)	1986-10-22
BR8507011A (pt)	1987-01-06
AU4962385A (en)	1986-05-15
KR870700616A (ko)	1987-12-30
IL76847A0 (en)	1986-02-28

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DE69304057T2 (de)	1997-02-06	Indole fungizide
DE60032483T2 (de)	2007-04-19	Diamid-derivate von heterocyclischen dicarbonsäuren, insektizide für acker- und gartenbau und ein verfahren zu ihrer verwendung
JPH03169842A (ja)	1991-07-23	Ｎ―（置換ベンジルオキシ）イミン誘導体及びその製造方法、その用途並びにその使用方法
JPS6244521B2 (pt)	1987-09-21
KR0135974B1 (ko)	1998-04-25	테트라히드로피리미딘 화합물, 이의 제조 방법 및 이를 함유하는 해충 방제 조성물
US4792565A (en)	1988-12-20	Pyrazolecarbonylamine derivatives and agricultural and horticultural fungicides containing said compounds
JPH03135963A (ja)	1991-06-10	置換α‐ピリミジニルオキシ（チオ）‐およびα‐トリアジニルオキシ（チオ）カルボン酸誘導体、その製造方法、それを含有する除草、殺菌および植物成長制御作用を有する薬剤ならびにその薬剤の製造方法
JPH0539272A (ja)	1993-02-19	ピリミジンジオン誘導体および除草剤
JPH026476A (ja)	1990-01-10	フエニルピリミジノン誘導体、その製造方法、その中間体及び殺虫、殺ダニ剤組成物
JPS62500588A (ja)	1987-03-12	置換アミノ除草剤製造の改良方法
JPH08217777A (ja)	1996-08-27	２−ピラゾリン−５−オン誘導体及びその中間体並びに除草剤
JPH05202031A (ja)	1993-08-10	Ｎ−アミノピリミジンジオン誘導体および除草剤
JPH03197460A (ja)	1991-08-28	殺虫性ニトロ置換ヘテロ環式化合物
KR19990001101A (ko)	1999-01-15	캐테콜 아미노산 유도체, 이의 제조방법 및 그를 함유한 약제 조성물
CA1252468A (en)	1989-04-11	Herbicidal 5-amino-3-oxo-4-(substituted-phenyl)-2,3- dihydrofuran and derivatives thereof
JP3122811B2 (ja)	2001-01-09	置換アミノキナゾリノン（チオン）誘導体又はその塩類、その中間体及び有害生物防除剤並びにその使用方法
US5889027A (en)	1999-03-30	3(2H)-furanone derivatives
US4606756A (en)	1986-08-19	Herbicidal 2-(nitrogen heterocycle)5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofurans
JP3041957B2 (ja)	2000-05-15	Ｎ−フェニルテトラヒドロフタラミン酸誘導体およびその製造法ならびにそれを有効成分とする除草剤
JPH06192252A (ja)	1994-07-12	ピラジン誘導体および除草剤
KR930007422B1 (ko)	1993-08-10	제초성 2-(치환된-페닐)-3-아미노-2-사이클로펜테논 유도체의 제조방법
CS247091B2 (en)	1986-11-13	Antifungicide agent for appliaction in the agriculture and production method of its affective compounds
JPS63301884A (ja)	1988-12-08	有害生物防除化合物
JP3054977B2 (ja)	2000-06-19	殺菌性フラノン誘導体
US4723031A (en)	1988-02-02	Processes for synthesizing substituted and unsubstituted aminoacetate esters